DE30329C - Process for the preparation of substituted benzaldehydes and substituted indigo. (Partly dependent on patent 19768.) - Google Patents
Process for the preparation of substituted benzaldehydes and substituted indigo. (Partly dependent on patent 19768.)Info
- Publication number
- DE30329C DE30329C DENDAT30329D DE30329DA DE30329C DE 30329 C DE30329 C DE 30329C DE NDAT30329 D DENDAT30329 D DE NDAT30329D DE 30329D A DE30329D A DE 30329DA DE 30329 C DE30329 C DE 30329C
- Authority
- DE
- Germany
- Prior art keywords
- substituted
- indigo
- preparation
- benzaldehydes
- partly dependent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- HUMNYLRZRPPJDN-UHFFFAOYSA-N Benzaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 title claims description 11
- 235000000177 Indigofera tinctoria Nutrition 0.000 title claims description 11
- 229940097275 Indigo Drugs 0.000 title claims description 10
- 230000001419 dependent Effects 0.000 title claims description 4
- 150000003935 benzaldehydes Chemical class 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 240000007871 Indigofera tinctoria Species 0.000 title 1
- 241001062009 Indigofera Species 0.000 claims description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 229940095076 benzaldehyde Drugs 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- NDOPHXWIAZIXPR-UHFFFAOYSA-N 2-bromobenzaldehyde Chemical compound BrC1=CC=CC=C1C=O NDOPHXWIAZIXPR-UHFFFAOYSA-N 0.000 claims 2
- FPYUJUBAXZAQNL-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical compound ClC1=CC=CC=C1C=O FPYUJUBAXZAQNL-UHFFFAOYSA-N 0.000 claims 1
- 238000005893 bromination reaction Methods 0.000 claims 1
- -1 bromo- Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 238000005660 chlorination reaction Methods 0.000 claims 1
- 125000001309 chloro group Chemical class Cl* 0.000 claims 1
- 239000012024 dehydrating agents Substances 0.000 claims 1
- 238000005121 nitriding Methods 0.000 claims 1
- 230000001131 transforming Effects 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- SRWILAKSARHZPR-UHFFFAOYSA-N 3-chlorobenzaldehyde Chemical compound ClC1=CC=CC(C=O)=C1 SRWILAKSARHZPR-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-Chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- MMCPOSDMTGQNKG-UHFFFAOYSA-N Anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 1
- CAHQGWAXKLQREW-UHFFFAOYSA-N Benzal chloride Chemical compound ClC(Cl)C1=CC=CC=C1 CAHQGWAXKLQREW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 210000002268 Wool Anatomy 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- SURQXAFEQWPFPV-UHFFFAOYSA-L iron(2+) sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Fe+2].[O-]S([O-])(=O)=O SURQXAFEQWPFPV-UHFFFAOYSA-L 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- TWXTWZIUMCFMSG-UHFFFAOYSA-N nitride(3-) Chemical compound [N-3] TWXTWZIUMCFMSG-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B7/00—Indigoid dyes
- C09B7/02—Bis-indole indigos
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/08—Preparation of nitro compounds by substitution of hydrogen atoms by nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
inin
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Stje'tteetfe depends on the patent Μτ. .19 768,
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etfe abhängg
12; Ssunt 1883etfe dependent
12; Ssunt 1883
patengodparents
KAISERLICHESIMPERIAL
KLASSE 22: Farbstoffe, Firnisse,CLASS 22: dyes, varnishes,
Dr. h. Müller in hersfeld.Dr. H. Müller in hersfeld.
Verfahren zur Herstellung von substituirten Benzaldehyden und von substituirtem Indigo.Process for the preparation of substituted benzaldehydes and substituted indigo.
Theilweise abhängig vom Patent No. 19768. Patentirt im Deutschen Reiche vom 12. Juni 1883 ab.Partly dependent on patent no. 19768. Patented in the German Empire on June 12, 1883.
Chlorirt man Benzaldehyd bei Gegenwart von wasserentziehenden Körpern, z. B. Schwefelsäure mit oder ohne Jod, so erhält man Metachlorb enzaldehyd.If benzaldehyde is chlorinated in the presence of dehydrating bodies, e.g. B. sulfuric acid with or without iodine, one obtains metachlorobenzaldehyde.
Dieses Metachlorbenzaldehyd ist eine farblose, bei 206° siedende Flüssigkeit vom spec. Gew. 1,246 bei 150 C, deren Geruch demjenigen des reinen Benzaldehyd? sehr ähnlich ist. Beim Nitriren dieses Metachlorbenzaldehyds mit Salpetersäure, Salpeter und Schwefelsäure entsteht vorzugsweise Metachlororthonitrobenzaldehyd, das aus der Nitrirmischung mit Eiswasser ausfällt und wiederholt aus Alkohol krystallisirt, gelbliche Nadeln bildet, die bei 6o° schmelzen. Löst man dieses Metachlororthonitrobenzaldehyd in Aceton, versetzt diese Lösung mit etwas Wasser und dann mit verdünnter Natronlauge, so scheidet die Lösung nach kurzer Zeit Chlorindigo ab.This metachlorobenzaldehyde is a colorless liquid of spec. Weight 1.246 at 15 0 C, whose odor is that of pure benzaldehyde? is very similar. When this metachlorobenzaldehyde is nitrided with nitric acid, nitric acid, and sulfuric acid, metachlorothonitrobenzaldehyde is formed, which precipitates from the nitride mixture with ice water and repeatedly crystallizes from alcohol, forming yellowish needles which melt at 60 °. If this metachlorothonitrobenzaldehyde is dissolved in acetone, a little water is added to this solution and then diluted sodium hydroxide solution, the solution separates out chlorine indigo after a short time.
Der so erhaltene Chlorindigo ist dem reinen Indigo täuschend ähnlich; er ist ein tiefblaues, unter dem Mikroskop krystallinisches Pulver mit kupferrothem Strich, geschmack- und geruchlos, unlöslich in den gewöhnlichen Lösungsmitteln (Wasser, Alkohol, Aether, verdünnten Säuren und Alkalien), etwas löslich in heifsem Chloroform, Anilin und Benzalchlorid. Beim Erhitzen sublimirt er unter theilweiser Zersetzung. Beim Destilliren mit Natronhydrat zerfällt er in Kohlensäure und Chloranilin. Mit concentrirter Schwefelsäure bildet er eine in Wasser lösliche Sulfosäure, welche Wolle blau färbt. Durch reducirende Körper, wie Eisenvitriol und Alkalien, entsteht aus dem Chlorindigo eine Küpe, die wie die Küpe des gewöhnlichen Indigos verwendet werden kann.The chlorine indigo thus obtained is deceptively similar to pure indigo; he is a deep blue, under the microscope crystalline powder with a copper-red streak, tasteless and odorless, insoluble in common solvents (water, alcohol, ether, diluted Acids and alkalis), somewhat soluble in hot chloroform, aniline and benzal chloride. At the When heated it sublimates with partial decomposition. When distilling with sodium hydroxide it breaks down into carbonic acid and chloroaniline. With concentrated sulfuric acid it forms one Sulphonic acid soluble in water, which stains wool blue. By reducing bodies, like Iron vitriol and alkalis, the chlorine indigo creates a vat that, like the vat of the ordinary indigos can be used.
Entzieht man dem Chlorindigo das Chlor durch Wasserstoff im Entstehungszustande, so erhält man Indigo.If the chlorine is removed from the chlorine indigo by means of hydrogen in the state of formation, then one obtains indigo.
Wendet man anstatt des Chlors Brom an, so erhält man die entsprechenden Brdmderivate.If bromine is used instead of chlorine, the corresponding bromine derivatives are obtained.
Claims (3)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE30329C true DE30329C (en) |
Family
ID=306458
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT30329D Expired - Lifetime DE30329C (en) | Process for the preparation of substituted benzaldehydes and substituted indigo. (Partly dependent on patent 19768.) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE30329C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999038833A1 (en) * | 1998-02-02 | 1999-08-05 | Bromine Compounds Ltd. | Process for the halogenation of aldehydes and ketones |
| WO2017223369A1 (en) * | 2016-06-22 | 2017-12-28 | Vf Jeanswear Lp | Modified indigo compounds and methods of dyeing a substrate using a modified indigo compound |
-
0
- DE DENDAT30329D patent/DE30329C/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999038833A1 (en) * | 1998-02-02 | 1999-08-05 | Bromine Compounds Ltd. | Process for the halogenation of aldehydes and ketones |
| WO2017223369A1 (en) * | 2016-06-22 | 2017-12-28 | Vf Jeanswear Lp | Modified indigo compounds and methods of dyeing a substrate using a modified indigo compound |
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